EP2252165A2 - Use of alternan as texturizing agent in foodstuffs and cosmetics - Google Patents

Use of alternan as texturizing agent in foodstuffs and cosmetics

Info

Publication number
EP2252165A2
EP2252165A2 EP09717886A EP09717886A EP2252165A2 EP 2252165 A2 EP2252165 A2 EP 2252165A2 EP 09717886 A EP09717886 A EP 09717886A EP 09717886 A EP09717886 A EP 09717886A EP 2252165 A2 EP2252165 A2 EP 2252165A2
Authority
EP
European Patent Office
Prior art keywords
alternan
homogeneous composition
oil
cream
fat
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP09717886A
Other languages
German (de)
French (fr)
Other versions
EP2252165B9 (en
EP2252165B1 (en
Inventor
Claus Frohberg
Jens Pilling
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP12169201.6A priority Critical patent/EP2491798B1/en
Priority to EP09717886A priority patent/EP2252165B9/en
Priority to DK12169201.6T priority patent/DK2491798T3/en
Publication of EP2252165A2 publication Critical patent/EP2252165A2/en
Application granted granted Critical
Publication of EP2252165B1 publication Critical patent/EP2252165B1/en
Publication of EP2252165B9 publication Critical patent/EP2252165B9/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/98Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin
    • A61K8/981Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin of mammals or bird
    • A61K8/986Milk; Derivatives thereof, e.g. butter
    • AHUMAN NECESSITIES
    • A21BAKING; EDIBLE DOUGHS
    • A21DTREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
    • A21D2/00Treatment of flour or dough by adding materials thereto before or during baking
    • A21D2/08Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
    • A21D2/14Organic oxygen compounds
    • A21D2/18Carbohydrates
    • AHUMAN NECESSITIES
    • A21BAKING; EDIBLE DOUGHS
    • A21DTREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
    • A21D2/00Treatment of flour or dough by adding materials thereto before or during baking
    • A21D2/08Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
    • A21D2/14Organic oxygen compounds
    • A21D2/18Carbohydrates
    • A21D2/183Natural gums
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23CDAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00Milk preparations; Milk powder or milk powder preparations
    • A23C9/12Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • A23C9/137Thickening substances
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A23D7/0053Compositions other than spreads
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A23D7/0056Spread compositions
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23GCOCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G1/00Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/30Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/32Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds
    • A23G1/40Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23GCOCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/36Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
    • A23G3/42Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/60Salad dressings; Mayonnaise; Ketchup
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/20Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
    • A23L29/269Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of microbial origin, e.g. xanthan or dextran
    • A23L29/273Dextran; Polysaccharides produced by leuconostoc
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115Fatty acids or derivatives thereof; Fats or oils
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/20Reducing nutritive value; Dietetic products with reduced nutritive value
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/20Reducing nutritive value; Dietetic products with reduced nutritive value
    • A23L33/21Addition of substantially indigestible substances, e.g. dietary fibres
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L7/00Cereal-derived products; Malt products; Preparation or treatment thereof
    • A23L7/10Cereal-derived products
    • A23L7/117Flakes or other shapes of ready-to-eat type; Semi-finished or partly-finished products therefor
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23VINDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00Food compositions, function of food ingredients or processes for food or foodstuffs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10General cosmetic use
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/49Solubiliser, Solubilising system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59Mixtures
    • A61K2800/592Mixtures of compounds complementing their respective functions

Definitions

  • the present invention is directed to the use of alteman as texturizing agent, particularly as fat or oil replacer in foodstuffs or cosmetic preparations, a homogeneous composition comprising alternan and water, the use of the homogeneous composition as texturizing agent in foodstuffs or cosmetic preparations, and foodstuffs and cosmetic preparations comprising alternan as texturizing agent or a homogeneous composition comprising alternan.
  • WO2007/128559 and WO2007/128559 teach that very long chain inulins are efficient texturizing agents and fat replacers, especially in dairy products and ice cream.
  • the present invention is directed to the use of alternan as a texturizing agent in foodstuffs or cosmetic preparations.
  • the present invention is directed to the use of alternan as an emulsifier, preferably for foodstuffs and cosmetic preparations.
  • a texturizing agent according to the present invention imparts texture to foodstuffs or cosmetic preparations or modifies the texture of foodstuffs or cosmetic preparations.
  • texture refers to the properties held and sensations caused by the external surface of foodstuffs or cosmetic preparations received through the sense of touch.
  • mouthfeel is used alternatively to the term “texture” and both terms are used herein interchangeably with respect to foodstuffs.
  • texture is the skin feel of a cosmetic preparation.
  • alternan is a very suitable fat or oil replacer in foodstuffs.
  • the fat or oil component of foodstuffs has usually a major impact on its texture/mouthfeel, organoleptic characteristics, and flavor.
  • a fat or oil content usually imparts a creamy and smooth mouthfeel to a foodstuff.
  • Alternan is a polysaccharide composed of glucose units.
  • the glucose units are linked to each other via a- 1,3- and a- 1 ,6-glycosidic bonds, and said two types of bonds predominantly appear alternatingly.
  • Alternan may contain branches (Seymour et al, Carbohydrate Research
  • Alternan according to the present invention preferably has a weight average molecular weight Mw in the range of 10 000 000 g/mol to 60 000 000 g/mol (determined with GPC MALLS), more preferably in the range of 12 000 000 g/mol to 50 000 000 g/mol.
  • alternan is produced with altemansucrase originating from Leuconostoc Mesenteroides as described in WO 00/47727 and shows a weight average molecular weight Mw in the range of 33 000 000 g/mol to 60 000 000 g/mol (determined with GPC MALLS), more preferably in the range of 33 000 000 g/mol to 50 000 000 g/mol.
  • alternan is produced with truncated altemansucrase enzyme as described in PCT/EP2008/051760 and shows a weight average molecular weight Mw in the range of 12 000 000 g/mol to 30 000 000 g/mol (GPC MALLS), more preferably in the range of 14 000 000 g/mol to 28 000 000 g/mol, still more preferably in the range of 16 000 000 g/mol to 26 000 000 g/mol, most preferably 19 000 000 g/mol to 23 000 000 g/mol.
  • Truncated altemansucrase enzymes, methods for producing alternan therefrom as well as the alternan itself are described in PCT/EP2008/051760, which is incorporated herein by reference in its entirety.
  • a preferred foodstuff wherein alternan is used as a fat replacer is selected from dairy products, yoghurts, ice creams, milk-based soft ice, milk-based garnishes, puddings, cream, whipped cream, chocolate cream, butter cream, creme fraiche, curd, milk, such as skim milk, buttermilk, soured milk, kefir, milkshakes, egg custard, cheese, , such as cream cheese, soft cheese, sliced cheese, hard cheese, nutrition bars, energy bars, breakfast bars, confectionery, bakery products, crackers, cookies, biscuits, cereal chips, snack products, diet drinks, finished drinks, sports drinks, stamina drinks, powdered drink mixtures for dietary supplementation, infant and baby foodstuff, bread, croissants, breakfast cereals, spreads, sugar-free biscuits and chocolates, calcium chews, meat products, sausages, mayonnaise, dressings, nut butter, deep- frozen meals, sauces, gravy, soups, shortenings, canned foods and ready-to-serve meals.
  • the level of alteman in the foodstuff depends on the kind of foodstuff. Usually, alteran is used in an amount which is sufficient to reach the desired degree of fat/oil replacement and the desired mouthfeel properties.
  • exemplary levels of alteman in foodstuffs are 0,1 - 10 weight percent, more preferably 0,1 - 5 weight percent, and most preferably 0,1 - 3 weight percent, based on the total weight of all components forming the foodstuff.
  • Oils and fats may be wholly substituted with alteman. However, a preferred degree of substitution is 20 to 80% by weight based on weight of the oils and/or fats.
  • the present invention is directed to a foodstuff comprising alternan as texturizing agent, particularly as a fat or oil replacer.
  • the foodstuff is preferably selected from the above mentioned foodstuffs
  • the term "foodstuff according to the invention also encompasses beverages.
  • the present invention is also directed to a cosmetic preparation, comprising alternan as texturizing agent.
  • the cosmetic preparation where alternan may be employed include, but are not limited to, deodorants, antiperspirants, antiperspirant/deodorants, shaving products, skin creams and lotions, moisturizers, toners, bath products, cleansing products, hair care products such as shampoos, conditioners, mousses, styling gels, nails creams and lotions, cuticle softeners, protective creams such as sunscreen, anti-aging products, and other personal care formulations.
  • the present invention is directed to a homogeneous composition comprising alternan and water.
  • homogeneous composition means that the composition shows no visible phase separation or separation of its constituents (not visible to the naked eye).
  • the homogeneous composition can show a wide viscosity range. So, the homogeneous composition may be a liquid or a more viscous cream, wherein a cream is preferred.
  • the composition according to the invention comprises 5 - 15 weight-% alternan and 85 - 95 weight-% water, based on the total weight of the composition, more preferably 8 - 13 weight-% alternan and 87 - 92 weight-% water. Further components may be included, such as surfactants and salts.
  • a homogeneous composition in another embodiment, comprises alternan, water and at least one fat or oil or a mixture of fat(s) and oil(s).
  • Said homogeneous composition comprising alternan, water and at least one fat and/or oil shows no visible phase separation between the fat or oil component and the water component (not visible to the naked eye).
  • said composition comprising alternan, water and at least one fat and/or oil may also be designated as an emulsion.
  • said homogeneous composition can show a wide viscosity range. So, the homogeneous composition may be a liquid or a more viscous cream, wherein a cream is preferred.
  • a composition comprises 5 - 15 weight-% alternan, 70 - 90 weight-% water, 5 - 15 weight-% fat or oil, more preferably 8 - 13 weight-% alternan, 74 - 84 weight- % water, and 8 - 13 weight-% fat or oil, based on the total weight of the composition. Further components such as surfactants and salts may be included.
  • Preferred fats/oils as a component for a homogeneous composition comprising alternan, water and at least one fat and/or oil are selected from arachidic oil, avocado oil, cotton seed oil, safflower oil, peanut oil, hazelnut oil, hemp oil, jojobaoil, camenillia oil, cocoa butter, coconut oil, pumpkin oil, linseed oil, macadamia nut oil, corn germ oil, almond oil, mango seed fat, poppy seed oil, evening primrose oil, olive oil, palm oil, palm kernel oil, papaya oil, pistachio nut oil, pecan nut oil, rapeseed oil, castor oil, mustard seed oil, sesame oil, shea butter, soybean oil, sunflower oil, walnut oil, water melonseed oil, grapeseed oil, wheat germ oil, cedarwood oil, wherein said oils might optionally be hardened oils.
  • the present invention is directed to a homogeneous composition comprising alternan and milk.
  • said composition comprises 5 - 15 weight-% alternan and 85 - 95 weight-% milk, based on the total weight of the composition, more preferably 8 - 13 weight-% alternan and 87 - 92 weight-% milk.
  • Further components may be included, such as surfactants and salts.
  • a cream comprising alternan and milk might preferably be used for all kind of dairy products.
  • the viscosity of a homogeneous composition according to the invention is adapted to the desired kind of foodstuff or cosmetic preparation, i.e. to the desired final viscosity of said foodstuff or cosmetic.
  • the homogeneous composition is preferably a cream, wherein a preferred range of viscosity of a cream is from 0.5 to 1.5 Pa*s, more preferably 0.8 to 1.3 Pa*s at 2O 0 C and a shear rate of 40 s '1 .
  • compositions preferably creams
  • cream according to the invention All of the above described homogeneous compositions, preferably creams, are hereinafter also designated as "(homogeneous) composition according to the invention” or “cream according to the invention”.
  • the present invention also relates to a method for preparing the above described compositions, the method comprising a) giving alternan and water into a vessel b) applying shear to obtain a homogeneous composition, and optionally c) adding oil or fat and applying shear to obtain a homogeneous composition.
  • the optional step c) relates to the above described embodiment of a homogeneous composition, comprising alternan, water and oil or fat.
  • steps b) and c) are preferably done under high shear with commonly known devices for such purpose, such as Ultra Turrax® dispersing tool from IKA company.
  • steps a) and b) are performed simultaneously, e.g. by adding alternan as a powder to water with simultaneous application of high shear.
  • Optional components as salts and emulsifiers might be added at any stage of the preparation.
  • the present invention is related to the use of a homogeneous composition as described above for the manufacture of foodstuffs or cosmetic preparations.
  • said homogeneous compositions preferably creams, can preferably used for above-listed foodstuffs and cosmetics.
  • homogeneous compositions can be used as constituent for foodstuffs or cosmetic preparations.
  • homogeneous compositions according to the present invention can fulfill, without limitation, following functions: giving body to foodstuffs or cosmetic preparations, act as a base for foodstuffs or cosmetic preparations, act as a texturizing agent for foodstuffs or cosmetic preparations.
  • the homogeneous compositions according to the present invention can fulfill one or more of the aforementioned functions.
  • the homogeneous compositions according to the present invention are preferably used as a fat or oil replacer in foodstuffs.
  • the homogeneous composition is preferably a cream.
  • the preferred foodstuffs for said use are selected from dairy products, yoghurts, ice creams, milk-based soft ice, milk-based garnishes, puddings, cream, whipped cream, chocolate cream, butter cream, creme fraiche, curd, milkshakes, egg custard, cheese, such as cream cheese, soft cheese, sliced cheese, hard cheese, nutrition bars, energy bars, breakfast bars, confectionery, bakery products, crackers, cookies, biscuits, cereal chips, snack products, infant and baby foodstuff, bread, croissants, spreads, sugar-free biscuits and chocolates, calcium chews, meat products, sausages, mayonnaise, dressings, nut butter, deep-frozen meals, sauces, gravy, soups, shortenings, canned foods and ready-to-serve meals.
  • Homogeneous compositions according to the invention have a texture similar to oils or fats.
  • this composition for example in dressings, mayonnaise, fresh cream, cream cheese, butter, salad oil, etc., in various cooked and processed food, the number of calories in the resulting food are greatly reduced.
  • Oils and fats may be wholly substituted with a homogeneous composition according to the present invention. However, a preferred degree of substitution is 20 to 80% by weight based on the oils and fats.
  • the present invention is also directed to a foodstuff or cosmetic preparation, characterized in that during its manufacturing process a homogeneous composition according to the present invention was added as a constituent.
  • a homogeneous composition according to the present invention preferably fulfills the functions as described above with respect to its use.
  • the homogeneous composition might be present in the final product without substantial structural alteration. This might for example be the case when a cream of the invention is used as the base for a cosmetic preparation and only some active ingredients are added.
  • the final foodstuff or cosmetic preparation is characterized in that it still comprises the cream. In other cases, e.g.
  • the cream in products which are heat treated after addition of the cream, the cream might be subjected to major alterations in its structure.
  • the present invention is to be understood to encompass all foodstuffs and cosmetic preparations during whose manufacturing process a cream according to the invention was added, regardless of whether the initial structure of the cream is altered in the final product or not.
  • Plasmid pAI-B-AlSu Q29 was transformed in E. coli DH5 ⁇ .
  • Vector pAI-B-AlSu contains the full-length coding sequence of altemansucrase derived from Leuconostoc mesenteroides strain NRRL B-1355 (cf. WO 00/47727), lacking the N-terminal 39 amino acids from the signal peptide, fused to an octapeptide strep-tag at the C-terminal end.
  • the strep-tag is linked to the protein through a dipeptide linker.
  • Expression of altemansucrase is under the transcriptional control of the tetA promoter/operator and repressor.
  • the tetA promoter is tightly regulated by the tet repressor which is encoded on the same plasmid and is constitutively expressed from the ⁇ -lactamase promoter. In this way, expression of altemansucrase is stringently repressed until efficient chemical induction by tetracycline or anhydrotetracycline, AHT.
  • the cells were pre-cultured in mineralmedium (Horn et al, 1996) with 100 ⁇ g/ml Ampicillin and 10% LB medium. Mineralmedium, without LB, was inoculated with this pre-culture.
  • the cells were grown at 37°C, induced with Anhydrotetracyclin (AHT) (0.2 mg/L), and grown further at 25°C.
  • AHT Anhydrotetracyclin
  • the cells were harvested, resuspended in [10 mM MOPS pH 7,6; 2,5 mM CaC12 und 0,05 % Trition X-100] and extracted with a high pressure homogenisator.
  • the cell lysate was centrifuged at 20 000 rpm for 20 minutes at 4°C. The supernatant was filtered over a 0.22 ⁇ m filter.
  • Alteman was produced in a 60 L Biotransformation containing 0.13% Acetic Acid, 100 mM NaAc pH5.3, 20% Sucrose, 1 mM DTT, 1600 ml filtered protein extract (ca. 3900 Units).
  • the reaction mixture was incubated for 60h. at 37°C.
  • the polymer was precipitated with 6OL Technical Ethanol 40 h 4 0 C, washed 2x with 60 L 60% Technical Ethanol, and Ix with 60 L 60% Ethanol Absolute.
  • the product was dried through lyophilization
  • the objective was to test the alternan as produced in example 1 (hereinafter "altenan") as a fat replacer in a model mayonnaise type dressing system.
  • a model mayonnaise dressing was developed with the control mayonnaise at 68 % oil (the standard of identity for mayonnaise is > 65 % oil).
  • Fat replacement levels of 25 % to 50 % were tested.
  • Example temperatures ranged from 3,3 to 6,TC. Viscosity was measured with a Brookfield RV at Speed 10 with Spindle #5 or 6, the reading was recorded after 1 minute.
  • a cream was prepared with water, 10 % of the alternan and 9.09 % Soybean Oil
  • the formula and process for preparing the alternan cream worked well.
  • the cream was white with a medium viscosity.
  • the dressings prepared with the alternan cream were much thinner than the control.
  • the test product with a 25 % reduction in oil had some viscosity and was similar to a pourable style dressing.
  • the Test product with a 50 % reduction in oil was very thin. The level of alternan may have been too low.
  • Test Method 2 The alternan powder was dry blended with the sugar, salt and mustard. The Control procedure was then followed. A 50 % reduction in fat was tested using 10 % alternan and 5 % alternan. The amount of water in the formula was adjusted to compensate for the reduction in oil and the addition of the alternan to balance the formula to 100 %.
  • the 10 % level of alternan was too high for this application. It was very difficult to incorporate the alternan into the egg mixture and a foodstuff processor to mix the mayonnaise had to be used. The resulting product was more like a shortening or spread than a spoonable dressing. The 5 % level worked well with the method as described and the resulting product was similar to Control with respect to appearance, texture and viscosity.
  • the method worked well to prepare the alternan cream and it blended into the egg mixture easily.
  • the egg mixture was thick but flowable.
  • the finished mayonnaise was thicker than the control.
  • the alternan works well to replace 50 % of the fat in a spoonable dressing/mayonnaise system at a 5.0 % level. A lower level (3.4 %) did not add enough viscosity to be comparable to the control. At the 5.0 % level, a fairly large variation in the sample viscosity was found when producing a replicate sample on a different date and when using an alternate method.
  • the alternan was dry blended with other dry ingredients and then added to the egg mixture, resulting viscosities were 39,700 cps and 22,000 cps. However, when the alternan was first made into a cream and then incorporated into the egg mixture the resulting product viscosity was 68,000 cps.
  • the objective was to test the carbohydrate as a fat replacer in a model pourable dressing system. We initially tested a 50 % reduction in fat and tested several oil types. We later tested a further reduction in fat with one oil type.
  • the reference material selected was Avicel (FMC BioPolymers, microcrystalline cellulose and carboxymethyl cellulose), a carbohydrate commonly used in low and no fat salad dressings.
  • a "blank" dressing was also prepared with 50 % reduced oil but no alteman or avicel in order to determine the viscosity contribution of the xanthan and PGA gums.
  • the Avicel was tested at 0.5, 1.0 and 1.25 % but the highest level was closest in viscosity to the control (still lower).
  • An additional sample was also prepared as a reference in which the two gums were increased to levels recommended for a dressing of approximately 20 % oil (0.40 % xanthan gum and 0.25 % PGA).
  • samples with 10 % fat were prepared. At 10 % fat, the salad dressing would qualify for a low fat claim which is ⁇ 3.0 grams of fat per serving, serving size is 30 grams.
  • Two higher levels of alternan were tested: 6.5 % and 7.75 % (7.75 % was tested first and the sample was thicker than the control).
  • the samples were prepared as described previously. After preparation, the samples were refrigerated overnight and measured for viscosity. The samples were then allowed to come to ambient temperature and viscosity was checked again. We then put the samples at 37,8°C to test stability and evaluated at 3 and 7 days
  • the alternan works well to partially replace the fat in a reduced fat salad dressing.
  • the alternan acts to build back the viscosity which is lost when the oil is decreased.
  • the appearance and aroma of the test dressings was fairly comparable to the Control and the alternan may act to mask some of the pungent aroma.
  • the thickness of the dressing seemed to be related to the iodine value of the oil used, the lower the iodine value, the less double bonds, the thicker it would tend to be at refrigerated conditions.
  • the control dressing separated and the oil droplets were larger versus the test dressing with alternan which did not separate and had smaller oil droplets.
  • the objective was to test the alternan as a fat replacer in bakery goods. Two model systems (cookie and cake) were tested. For cookie the fat replacement was at 30% and for cake at 30% and 50%.
  • Testl Cookies with Alternan by method 1
  • Test2 Cookies with Alternan by method 2
  • Method 1 a) Full fat cake (control)
  • Method 2 a) Alternan reduced fat cookie (Test 4) - Making Alternan gel 24% (Alternan powder added to water and sheared with Ultra Turax at 11600 rpm for 5min)

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Food Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Nutrition Science (AREA)
  • Molecular Biology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Mycology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Inorganic Chemistry (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Microbiology (AREA)
  • Dispersion Chemistry (AREA)
  • Zoology (AREA)
  • Seasonings (AREA)
  • Cosmetics (AREA)
  • Confectionery (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Bakery Products And Manufacturing Methods Therefor (AREA)
  • Dairy Products (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Jellies, Jams, And Syrups (AREA)

Abstract

The invention is directed to the use of alternan as texturizing agent, particularly as fat or oil replacer in foodstuffs or cosmetic preparations, a homogeneous composition comprising alternan and water, the use of the homogeneous composition as texturizing agent in foodstuffs or cosmetic preparations, and foodstuffs and cosmetic preparations comprising alternan as texturizing agent or a homogeneous composition comprising alternan.

Description

Use of alternan as texturizing agent in foodstuffs and cosmetics
The present invention is directed to the use of alteman as texturizing agent, particularly as fat or oil replacer in foodstuffs or cosmetic preparations, a homogeneous composition comprising alternan and water, the use of the homogeneous composition as texturizing agent in foodstuffs or cosmetic preparations, and foodstuffs and cosmetic preparations comprising alternan as texturizing agent or a homogeneous composition comprising alternan.
In recent years, problems of obesity and hyperlipemia have increased due to excessive consumption of oils, fats, sugars, etc., and decreased consumption of dietary fibers. It has been suggested that certain adult diseases, which are leading causes of death, such as cancer, heart diseases, etc., are associated with excessive consumption of oils, fats, and sugars and decreased consumption of dietary fibers. For these reasons, low calorie foodstuffs wherein oil or fat is replaced by substances with beneficial texturizing properties have become popular.
Some Polysaccharides have been described as texturizing agents and fat replacers. US 5, 169,671 relates to a food or drink containing a fructose polymer mainly composed of beta- 2,1 -bond, referred to as "polyfructan", as a substitute for oils, fats, and sugars and having improved gel properties compared with foods containing other oil, fat, or sugar substitutes and a creamy taste and texture equivalent to that derived from oils and fats and a method of producing such a food or drink.
WO2007/128559 and WO2007/128559 teach that very long chain inulins are efficient texturizing agents and fat replacers, especially in dairy products and ice cream.
However, in view of the increased need for efficient texturizing agents and fat replacers for foods it was an object of the present invention to find alternative substances which can be used for this purpose
The present invention is directed to the use of alternan as a texturizing agent in foodstuffs or cosmetic preparations. In another aspect the present invention is directed to the use of alternan as an emulsifier, preferably for foodstuffs and cosmetic preparations.
A texturizing agent according to the present invention imparts texture to foodstuffs or cosmetic preparations or modifies the texture of foodstuffs or cosmetic preparations. The term "texture" refers to the properties held and sensations caused by the external surface of foodstuffs or cosmetic preparations received through the sense of touch.
In connection with foodstuffs, the term "mouthfeel" is used alternatively to the term "texture" and both terms are used herein interchangeably with respect to foodstuffs. In connection with cosmetic preparations, a major meaning of the term texture is the skin feel of a cosmetic preparation.
In the present invention it can be shown that alternan is a very suitable fat or oil replacer in foodstuffs. The fat or oil component of foodstuffs has usually a major impact on its texture/mouthfeel, organoleptic characteristics, and flavor. A fat or oil content usually imparts a creamy and smooth mouthfeel to a foodstuff. These desired properties of foodstuffs can also be reached by adding alteman to foodstuffs. The term "fat or oil replacer" in this connection means that at least a part of a fat or oil component in a foodstuff is removed from the foodstuff and replaced by alternan. The term "fat or oil replacer", however, can also mean that the total fat or oil component in a foodstuff is removed from the foodstuff and replaced by alternan.
Alternan is a polysaccharide composed of glucose units. The glucose units are linked to each other via a- 1,3- and a- 1 ,6-glycosidic bonds, and said two types of bonds predominantly appear alternatingly. Alternan may contain branches (Seymour et al, Carbohydrate Research
74, (1979), 41 -62). Alternan and methods for producing alternan are well known from the state of the art. See for example Jeanes et al. (1954) J. Am. Chem. Soc, 76: 5041-5052,
Misaki et al. (1980) Carbohydr. Res., 84: 273-285, Cote and Robyt (1982), Carbohydr. Res. , 101 : 57-74, Cote (1992), Carbohydrate Polymers 19, 249-252, WO 00/47727, US 5,702,942,
US20060127328, PCT/EP2008/051760.
Alternan according to the present invention preferably has a weight average molecular weight Mw in the range of 10 000 000 g/mol to 60 000 000 g/mol (determined with GPC MALLS), more preferably in the range of 12 000 000 g/mol to 50 000 000 g/mol. In a special embodiment, alternan is produced with altemansucrase originating from Leuconostoc Mesenteroides as described in WO 00/47727 and shows a weight average molecular weight Mw in the range of 33 000 000 g/mol to 60 000 000 g/mol (determined with GPC MALLS), more preferably in the range of 33 000 000 g/mol to 50 000 000 g/mol. In still another special embodiment, alternan is produced with truncated altemansucrase enzyme as described in PCT/EP2008/051760 and shows a weight average molecular weight Mw in the range of 12 000 000 g/mol to 30 000 000 g/mol (GPC MALLS), more preferably in the range of 14 000 000 g/mol to 28 000 000 g/mol, still more preferably in the range of 16 000 000 g/mol to 26 000 000 g/mol, most preferably 19 000 000 g/mol to 23 000 000 g/mol. Truncated altemansucrase enzymes, methods for producing alternan therefrom as well as the alternan itself are described in PCT/EP2008/051760, which is incorporated herein by reference in its entirety.
A preferred foodstuff wherein alternan is used as a fat replacer is selected from dairy products, yoghurts, ice creams, milk-based soft ice, milk-based garnishes, puddings, cream, whipped cream, chocolate cream, butter cream, creme fraiche, curd, milk, such as skim milk, buttermilk, soured milk, kefir, milkshakes, egg custard, cheese, , such as cream cheese, soft cheese, sliced cheese, hard cheese, nutrition bars, energy bars, breakfast bars, confectionery, bakery products, crackers, cookies, biscuits, cereal chips, snack products, diet drinks, finished drinks, sports drinks, stamina drinks, powdered drink mixtures for dietary supplementation, infant and baby foodstuff, bread, croissants, breakfast cereals, spreads, sugar-free biscuits and chocolates, calcium chews, meat products, sausages, mayonnaise, dressings, nut butter, deep- frozen meals, sauces, gravy, soups, shortenings, canned foods and ready-to-serve meals.
The level of alteman in the foodstuff depends on the kind of foodstuff. Usually, alteran is used in an amount which is sufficient to reach the desired degree of fat/oil replacement and the desired mouthfeel properties. Without limitation exemplary levels of alteman in foodstuffs are 0,1 - 10 weight percent, more preferably 0,1 - 5 weight percent, and most preferably 0,1 - 3 weight percent, based on the total weight of all components forming the foodstuff.
Oils and fats may be wholly substituted with alteman. However, a preferred degree of substitution is 20 to 80% by weight based on weight of the oils and/or fats. In a farther aspect the present invention is directed to a foodstuff comprising alternan as texturizing agent, particularly as a fat or oil replacer. The foodstuff is preferably selected from the above mentioned foodstuffs The term "foodstuff according to the invention also encompasses beverages.
The present invention is also directed to a cosmetic preparation, comprising alternan as texturizing agent. The cosmetic preparation where alternan may be employed include, but are not limited to, deodorants, antiperspirants, antiperspirant/deodorants, shaving products, skin creams and lotions, moisturizers, toners, bath products, cleansing products, hair care products such as shampoos, conditioners, mousses, styling gels, nails creams and lotions, cuticle softeners, protective creams such as sunscreen, anti-aging products, and other personal care formulations.
In a further aspect, the present invention is directed to a homogeneous composition comprising alternan and water. The term "homogeneous composition" means that the composition shows no visible phase separation or separation of its constituents (not visible to the naked eye).
Depending on the relative amounts of alternan and water, said homogeneous composition can show a wide viscosity range. So, the homogeneous composition may be a liquid or a more viscous cream, wherein a cream is preferred.
In one embodiment the composition according to the invention comprises 5 - 15 weight-% alternan and 85 - 95 weight-% water, based on the total weight of the composition, more preferably 8 - 13 weight-% alternan and 87 - 92 weight-% water. Further components may be included, such as surfactants and salts.
In another embodiment, a homogeneous composition according to the invention comprises alternan, water and at least one fat or oil or a mixture of fat(s) and oil(s). Said homogeneous composition comprising alternan, water and at least one fat and/or oil shows no visible phase separation between the fat or oil component and the water component (not visible to the naked eye). Thus, said composition comprising alternan, water and at least one fat and/or oil may also be designated as an emulsion. Depending on the relative amounts of alternan, water, and oil and/or fat, said homogeneous composition can show a wide viscosity range. So, the homogeneous composition may be a liquid or a more viscous cream, wherein a cream is preferred.
In one embodiment a composition comprises 5 - 15 weight-% alternan, 70 - 90 weight-% water, 5 - 15 weight-% fat or oil, more preferably 8 - 13 weight-% alternan, 74 - 84 weight- % water, and 8 - 13 weight-% fat or oil, based on the total weight of the composition. Further components such as surfactants and salts may be included.
Preferred fats/oils as a component for a homogeneous composition comprising alternan, water and at least one fat and/or oil are selected from arachidic oil, avocado oil, cotton seed oil, safflower oil, peanut oil, hazelnut oil, hemp oil, jojobaoil, camenillia oil, cocoa butter, coconut oil, pumpkin oil, linseed oil, macadamia nut oil, corn germ oil, almond oil, mango seed fat, poppy seed oil, evening primrose oil, olive oil, palm oil, palm kernel oil, papaya oil, pistachio nut oil, pecan nut oil, rapeseed oil, castor oil, mustard seed oil, sesame oil, shea butter, soybean oil, sunflower oil, walnut oil, water melonseed oil, grapeseed oil, wheat germ oil, cedarwood oil, wherein said oils might optionally be hardened oils.
In still another aspect, the present invention is directed to a homogeneous composition comprising alternan and milk. In a preferred embodiment said composition comprises 5 - 15 weight-% alternan and 85 - 95 weight-% milk, based on the total weight of the composition, more preferably 8 - 13 weight-% alternan and 87 - 92 weight-% milk. Further components may be included, such as surfactants and salts. A cream comprising alternan and milk might preferably be used for all kind of dairy products.
The viscosity of a homogeneous composition according to the invention is adapted to the desired kind of foodstuff or cosmetic preparation, i.e. to the desired final viscosity of said foodstuff or cosmetic. However, as said above, the homogeneous composition is preferably a cream, wherein a preferred range of viscosity of a cream is from 0.5 to 1.5 Pa*s, more preferably 0.8 to 1.3 Pa*s at 2O0C and a shear rate of 40 s'1.
All of the above described homogeneous compositions, preferably creams, are hereinafter also designated as "(homogeneous) composition according to the invention" or "cream according to the invention". The present invention also relates to a method for preparing the above described compositions, the method comprising a) giving alternan and water into a vessel b) applying shear to obtain a homogeneous composition, and optionally c) adding oil or fat and applying shear to obtain a homogeneous composition.
The optional step c) relates to the above described embodiment of a homogeneous composition, comprising alternan, water and oil or fat.
Mixing in steps b) and c) is preferably done under high shear with commonly known devices for such purpose, such as Ultra Turrax® dispersing tool from IKA company. In a preferred embodiment, steps a) and b) are performed simultaneously, e.g. by adding alternan as a powder to water with simultaneous application of high shear. Optional components as salts and emulsifiers might be added at any stage of the preparation.
In a further aspect, the present invention is related to the use of a homogeneous composition as described above for the manufacture of foodstuffs or cosmetic preparations. In this connection, said homogeneous compositions, preferably creams, can preferably used for above-listed foodstuffs and cosmetics.
According to the present invention the homogeneous compositions can be used as constituent for foodstuffs or cosmetic preparations. In this connection, homogeneous compositions according to the present invention can fulfill, without limitation, following functions: giving body to foodstuffs or cosmetic preparations, act as a base for foodstuffs or cosmetic preparations, act as a texturizing agent for foodstuffs or cosmetic preparations. The homogeneous compositions according to the present invention can fulfill one or more of the aforementioned functions.
In regard to texturizing properties the homogeneous compositions according to the present invention are preferably used as a fat or oil replacer in foodstuffs. In this connection, the homogeneous composition is preferably a cream. The preferred foodstuffs for said use are selected from dairy products, yoghurts, ice creams, milk-based soft ice, milk-based garnishes, puddings, cream, whipped cream, chocolate cream, butter cream, creme fraiche, curd, milkshakes, egg custard, cheese, such as cream cheese, soft cheese, sliced cheese, hard cheese, nutrition bars, energy bars, breakfast bars, confectionery, bakery products, crackers, cookies, biscuits, cereal chips, snack products, infant and baby foodstuff, bread, croissants, spreads, sugar-free biscuits and chocolates, calcium chews, meat products, sausages, mayonnaise, dressings, nut butter, deep-frozen meals, sauces, gravy, soups, shortenings, canned foods and ready-to-serve meals.
Homogeneous compositions according to the invention have a texture similar to oils or fats. By substituting this composition for liquid oils and solid fats, for example in dressings, mayonnaise, fresh cream, cream cheese, butter, salad oil, etc., in various cooked and processed food, the number of calories in the resulting food are greatly reduced. Oils and fats may be wholly substituted with a homogeneous composition according to the present invention. However, a preferred degree of substitution is 20 to 80% by weight based on the oils and fats.
Finally, the present invention is also directed to a foodstuff or cosmetic preparation, characterized in that during its manufacturing process a homogeneous composition according to the present invention was added as a constituent. In the foodstuff or cosmetic, a homogeneous composition according to the present invention preferably fulfills the functions as described above with respect to its use. Depending on the kind of foodstuff or cosmetic and its manufacturing process, the homogeneous composition might be present in the final product without substantial structural alteration. This might for example be the case when a cream of the invention is used as the base for a cosmetic preparation and only some active ingredients are added. In such case, the final foodstuff or cosmetic preparation is characterized in that it still comprises the cream. In other cases, e.g. in products which are heat treated after addition of the cream, the cream might be subjected to major alterations in its structure. The present invention is to be understood to encompass all foodstuffs and cosmetic preparations during whose manufacturing process a cream according to the invention was added, regardless of whether the initial structure of the cream is altered in the final product or not.
In the following section, the present invention is further illustrated by examples, which are, however, not intended to limit the scope of the invention as defined in the appended claims. Examples
1. Manufacture of alternan
Plasmid pAI-B-AlSu Q29 was transformed in E. coli DH5α. Vector pAI-B-AlSu contains the full-length coding sequence of altemansucrase derived from Leuconostoc mesenteroides strain NRRL B-1355 (cf. WO 00/47727), lacking the N-terminal 39 amino acids from the signal peptide, fused to an octapeptide strep-tag at the C-terminal end. The strep-tag is linked to the protein through a dipeptide linker. Expression of altemansucrase is under the transcriptional control of the tetA promoter/operator and repressor. The tetA promoter is tightly regulated by the tet repressor which is encoded on the same plasmid and is constitutively expressed from the β-lactamase promoter. In this way, expression of altemansucrase is stringently repressed until efficient chemical induction by tetracycline or anhydrotetracycline, AHT.
The cells were pre-cultured in mineralmedium (Horn et al, 1996) with 100 μg/ml Ampicillin and 10% LB medium. Mineralmedium, without LB, was inoculated with this pre-culture. The cells were grown at 37°C, induced with Anhydrotetracyclin (AHT) (0.2 mg/L), and grown further at 25°C. The cells were harvested, resuspended in [10 mM MOPS pH 7,6; 2,5 mM CaC12 und 0,05 % Trition X-100] and extracted with a high pressure homogenisator. The cell lysate was centrifuged at 20 000 rpm for 20 minutes at 4°C. The supernatant was filtered over a 0.22 μm filter.
Alteman was produced in a 60 L Biotransformation containing 0.13% Acetic Acid, 100 mM NaAc pH5.3, 20% Sucrose, 1 mM DTT, 1600 ml filtered protein extract (ca. 3900 Units). The reaction mixture was incubated for 60h. at 37°C. The polymer was precipitated with 6OL Technical Ethanol 40 h 40C, washed 2x with 60 L 60% Technical Ethanol, and Ix with 60 L 60% Ethanol Absolute. The product was dried through lyophilization
Reference: Horn U, Strittmatter W, Krebber A, Knupfer U, Kujau M, Wenderoth R, Muller K, Matzku S, Pluckthun A, Riesenberg D. High volumetric yields of functional dimeric miniantibodies in Escherichia coli, using an optimized expression vector and high-cell-density fermentation under non-limited growth conditions. Appl Microbiol Biotechnol 1996; (46): 524-532.
2. Application tests
2.1 Mayonnaise
Background:
The objective was to test the alternan as produced in example 1 (hereinafter "altenan") as a fat replacer in a model mayonnaise type dressing system. A model mayonnaise dressing was developed with the control mayonnaise at 68 % oil (the standard of identity for mayonnaise is > 65 % oil).
Three methods of incorporating the alternan were evaluated:
1. Making an alternan cream and adding it in the last step after the oil.
2. Dry blending the alternan with dry ingredients and adding it to the egg mixture.
3. Making an alternan cream and adding it to the egg mixture.
After the initial experiments using Test Method 1 , it was determined that the level of alternan needed to be higher.
Fat replacement levels of 25 % to 50 % were tested.
Control Formula and Method:
Ingredients
Egg Mixture %
Egg Yolks 11.15 Water 9.17
Vinegar (Distilled White, 5 % Acidity) 8.78
Sugar 1.30
Salt 0.81
Mustard Powder 0.64 Mayonnaise
Egg Mixture (from above) 31.85
Salad Oil (Soybean) 68.15
The egg yolks, water, vinegar (5 % acidity), sugar, salt and dry mustard were mixed together and heated slowly until just beginning to boil.
The egg mixture was allowed to cool slightly and then soybean oil was sheared into the mixture using a Silverson High Shear mixer fitted with a Square Hole High Shear screen to form an emulsion.
The mayonnaise was refrigerated overnight before measuring the viscosity (sample temperatures ranged from 3,3 to 6,TC). Viscosity was measured with a Brookfield RV at Speed 10 with Spindle #5 or 6, the reading was recorded after 1 minute.
Test Method 1 :
Ingredients
Alternan Cream %
Water 80.91 alternan 10.0
Salad Oil (Soybean) 9.09
Mayonnaise 50 % Fat Repl. 25 % Fat Reol.
Egg Mixture (as described in Control) 31.85 31.85
Salad Oil (Soybean) 34.15 50.15
Alternan Cream 34.00 18.00
Final % of alternan in 50 % Fat Replaced Mayonnaise = 3.4 % Final % of alternan in 25 % Fat Replaced Mayonnaise = 1.8 %
" A cream was prepared with water, 10 % of the alternan and 9.09 % Soybean Oil
(using the Silverson High Shear mixer).
The mayonnaise was prepared as described in the Control method but after the addition of the Soybean Oil, the alternan Cream was sheared in. "Blank"
A sample with a 25 % reduction in oil was prepared by simply increasing the water (no alternan cream was added).
Results and Observations, Test Method 1 :
The formula and process for preparing the alternan cream worked well. The cream was white with a medium viscosity. However, the dressings prepared with the alternan cream were much thinner than the control. The test product with a 25 % reduction in oil had some viscosity and was similar to a pourable style dressing. The Test product with a 50 % reduction in oil was very thin. The level of alternan may have been too low.
Test Method 2: The alternan powder was dry blended with the sugar, salt and mustard. The Control procedure was then followed. A 50 % reduction in fat was tested using 10 % alternan and 5 % alternan. The amount of water in the formula was adjusted to compensate for the reduction in oil and the addition of the alternan to balance the formula to 100 %.
Results and Observations, Test Method 2:
The 10 % level of alternan was too high for this application. It was very difficult to incorporate the alternan into the egg mixture and a foodstuff processor to mix the mayonnaise had to be used. The resulting product was more like a shortening or spread than a spoonable dressing. The 5 % level worked well with the method as described and the resulting product was similar to Control with respect to appearance, texture and viscosity.
*Since the sample was so thick the viscosity measurement procedure was modified: the Brookfield with Heliopath Spindle F was used at speed 5.
Test Method 3
Ingredients
Egg Mixture %
Egg Yolks 1 1.15
Water 0
Vinegar (Distilled White, 5 % Acidity) 8.78
Alternan Cream* 48.25
Sugar 1.30
Salt 0.81
Mustard Powder 0.64 *Alternan Cream
Water 79.30 alternan 10.36
Salad Oil (Soybean) 10.34
Mayonnaise Egg Mixture 70.93 Salad Oil (Soybean) 29.07
Final level of alternan = 5 %
Alternan Cream
Add the alternan into the water slowly while shearing with the Silverson mixer. After all the alternan is incorporated, add the oil slowly until well blended. Follow the control procedure for the egg mixture but whisk the alternan Cream in last. Follow the control procedure for preparing the mayonnaise.
Results and Observations, Test Method 3 :
The method worked well to prepare the alternan cream and it blended into the egg mixture easily. The egg mixture was thick but flowable. The finished mayonnaise was thicker than the control.
Discussion and Conclusions:
The alternan works well to replace 50 % of the fat in a spoonable dressing/mayonnaise system at a 5.0 % level. A lower level (3.4 %) did not add enough viscosity to be comparable to the control. At the 5.0 % level, a fairly large variation in the sample viscosity was found when producing a replicate sample on a different date and when using an alternate method. When the alternan was dry blended with other dry ingredients and then added to the egg mixture, resulting viscosities were 39,700 cps and 22,000 cps. However, when the alternan was first made into a cream and then incorporated into the egg mixture the resulting product viscosity was 68,000 cps.
2.2 Pourable Dressing
Background:
The objective was to test the carbohydrate as a fat replacer in a model pourable dressing system. We initially tested a 50 % reduction in fat and tested several oil types. We later tested a further reduction in fat with one oil type. The reference material selected was Avicel (FMC BioPolymers, microcrystalline cellulose and carboxymethyl cellulose), a carbohydrate commonly used in low and no fat salad dressings.
Methods: Ingredients Control Test with alternan Reference
% % % Water 21.35 38.85 42.6
Xanthan Gum 0.25 0.25 0.25
Propylene Glycol Alginate 0.15 0.15 0.15 alternan 0.00 5.00 0.00
Avicel SD 3410 0.00 0.00 1.25 Salt 1.75 1.75 1.75
High Fructose Corn Syrup 21.0 21.0 21.0
Vinegar (120 grain) 10.5 10.5 10.5
Vegetable Oil 45.00 22.5 22.5 ■ Dry blend the gums (and alternan or Avicel) and add them to the water while shearing with the Silverson High Shear mixer.
Shear for 5 minutes. Add the salt, HFCS and vinegar and mix.
■ Slowly add the oil while shearing and shear for an additional 1.5 minutes after all the oil is added.
Note: a "blank" dressing was also prepared with 50 % reduced oil but no alteman or avicel in order to determine the viscosity contribution of the xanthan and PGA gums. The Avicel was tested at 0.5, 1.0 and 1.25 % but the highest level was closest in viscosity to the control (still lower). An additional sample was also prepared as a reference in which the two gums were increased to levels recommended for a dressing of approximately 20 % oil (0.40 % xanthan gum and 0.25 % PGA).
Results and Observations, Oil Comparison:
Stability Study
Several of the samples were tested for stability by putting them at 37,8°C and evaluating them at 3 and 7 days. Note that the Tuna Oil samples were not produced in time to include them in the study.
The following table summarizes the results of the stability test:
Further Reduced Fat Dressing
In order to determine if the alternan would work in further reducing the fat in the salad dressing, samples with 10 % fat (reduced from 45 %) were prepared. At 10 % fat, the salad dressing would qualify for a low fat claim which is < 3.0 grams of fat per serving, serving size is 30 grams. Two higher levels of alternan were tested: 6.5 % and 7.75 % (7.75 % was tested first and the sample was thicker than the control). The samples were prepared as described previously. After preparation, the samples were refrigerated overnight and measured for viscosity. The samples were then allowed to come to ambient temperature and viscosity was checked again. We then put the samples at 37,8°C to test stability and evaluated at 3 and 7 days
A table summarizing the results follows:
Discussion:
The alternan works well to partially replace the fat in a reduced fat salad dressing. The alternan acts to build back the viscosity which is lost when the oil is decreased. The appearance and aroma of the test dressings was fairly comparable to the Control and the alternan may act to mask some of the pungent aroma. There didn't seem to be an interaction between the alternan and the oil type. The thickness of the dressing seemed to be related to the iodine value of the oil used, the lower the iodine value, the less double bonds, the thicker it would tend to be at refrigerated conditions. There did seem to be a slight advantage to using the alternan in a fish oil containing dressing. The control dressing separated and the oil droplets were larger versus the test dressing with alternan which did not separate and had smaller oil droplets. The alternan containing dressings were able to stand up to some abuse (3 days at 37,8°C) some separation after 7 days at 37,8°C was seen. Even though there was some separation, the viscosities remained quite stable. We did note some shear thinning in the Test samples. When samples were allowed to "equilibrate" in a beaker the viscosity was higher versus if the sample was shaken just before the viscosity measurement. We didn't find this to the same extent with the Control dressing. It was possible to reduce the fat in the model dressing to 10 % or "low fat" by increasing the alternan to 6.5 %. The resulting dressing had similar characteristics to the Control with respect to viscosity and appearance. There was some slight separation after being stored at 37,8°C for 7 days but the viscosity remained quite consistent.
2.3 Bakery goods
Background:
The objective was to test the alternan as a fat replacer in bakery goods. Two model systems (cookie and cake) were tested. For cookie the fat replacement was at 30% and for cake at 30% and 50%.
Sugar snap cookie
Formula and methods
Method 1 :
a) Full fat cookie (control) - All solids (flour, sugar, soda, baking powder, salt, milk powder) were mixed in farinograph for 30 sec
- Shortening added and mixed for 1 min and 30 sec
- Water added and mixed for 2 min and 30 sec
- Dough rolled (height lcm) and 4 cookies cut with a cutter (76.2 mm) - Cookies placed on baking plan and baked at 193 °C for 10 min
b) Alternan reduced fat cookie
- As described in the control except that alternan powder was mixed with solids
Method 2:
a) Alternan reduced fat cookie
- Making Alternan gel 22% (Alternan powder added to water and sheared with Ultra Turax at 11600 rpm for 5 min)
- All solids (flour, sugar, soda, baking powder, salt, milk powder) were mixed in farinograph for 30 sec
- Shortening added and mixed for 1 min and 30 sec
- Alternan gel added and mixed for 2 min and 30 sec - Dough rolled (height 1 cm) and 4 cookies cut with a cutter (76.2 mm)
- Cookies placed on baking plan and baked at 193°C for lOmin
Results and observations:
Testl = Cookies with Alternan by method 1 Test2 = Cookies with Alternan by method 2
Cake (Sand cake)
Formulas and methods
Method 1 : a) Full fat cake (control)
- The solids (flour, salt, starch and baking powder were blended (mixture) - The shortening, sugar and vanilla sugar were mixed in a kitchen machine for 1 min
- The whisked eggs then added and mixed for 1 min
- The mixture was gradually added and mixed for 2 min
- 12O g of dough was placed in a baking pan and baked for 40 min at 1600C
b) Alternan reduced fat cake (Tests 1 to 3 and Test 5)
- As described in the control, except that alternan powder was mixed with solids
Method 2: a) Alternan reduced fat cookie (Test 4) - Making Alternan gel 24% (Alternan powder added to water and sheared with Ultra Turax at 11600 rpm for 5min)
- The solids (flour, salt, starch and baking powder were blended (mixture)
- The Alternan gel, shortening, sugar and vanilla sugar were mixed in a kitchen machine for lmin - The whisked eggs then added and mixed for 1 min
- The mixture was gradually added and mixed for 2 min
- 12Og of dough was placed in a baking pan and baked for 40 min at 1600C
Results and observations:
K)

Claims

Claims
1. Use of alternan as texturizing agent in foodstuffs or cosmetic preparations.
2. Use of alternan according to claim 1, wherein alteran is used as a fat or oil replacer in foodstuffs.
3. Foodstuff, comprising alternan as texturizing agent
4. Foodstuff according to claim 3, comprising alternan as a fat or oil replacer.
5. Foodstuff according to claim 3 or 4, which is selected from dairy products, yoghurts, ice creams, milk-based soft ice, milk-based garnishes, puddings, cream, whipped cream, chocolate cream, butter cream, creme fraiche, curd, milk, such as skim milk, buttermilk, soured milk, kefir, milkshakes, egg custard, cheese, , such as cream cheese, soft cheese, sliced cheese, hard cheese, nutrition bars, energy bars, breakfast bars, confectionery, bakery products, crackers, cookies, biscuits, cereal chips, snack products, diet drinks, finished drinks, sports drinks, stamina drinks, powdered drink mixtures for dietary supplementation, infant and baby foodstuff, bread, croissants, breakfast cereals, spreads, sugar-free biscuits and chocolates, calcium chews, meat products, sausages, mayonnaise, dressings, nut butter, deep-frozen meals, sauces, gravy, soups, shortenings, canned foods and ready-to-serve meals.
6. Cosmetic preparation, comprising alternan as texturizing agent.
7. Homogeneous composition comprising alternan and water.
8. Homogeneous composition according to claim 7, comprising: 5 - 15 weight-% alternan,
85 - 95 weight-% water.
9. Homogeneous composition according to claim 7, further comprising at least one fat or oil.
10. Homogeneous composition according to claim 9, comprising 5 - 15 weight-% alteman,
70 - 90 weight-% water, 5 - 15 weight-% fat and/or oil.
11. Homogeneous composition, comprising alternan and milk.
12. Homogeneous composition according to claim 11, comprising 5 - 15 weight-% alteman,
85 - 95 weight-% milk.
13. Method for preparing a homogeneous composition according to one of claims 7 - 10, the method comprising a) giving alternan and water into a vessel b) applying shear to obtain a homogeneous composition, and optionally c) adding oil and/or fat and applying shear to obtain a homogeneous composition.
14. Method for preparing a homogeneous composition according to claim 11 or 12, the method comprising a) giving alternan and milk into a vessel b) applying shear to obtain a homogeneous composition.
15. Use of a homogeneous composition according to one of claims 7-12, for the manufacture of foodstuffs or cosmetic preparations.
16. Use of a homogeneous composition according to claim 15, wherein the homogeneous composition is used as a fat or oil replacer in foodstuffs.
17. Use according to claim 15 or 16, wherein the foodstuff is selected from dairy products, yoghurts, ice creams, milk-based soft ice, milk-based garnishes, puddings, cream, whipped cream, chocolate cream, butter cream, creme fraiche, curd, milkshakes, egg custard, cheese, such as cream cheese, soft cheese, sliced cheese, hard cheese, nutrition bars, energy bars, breakfast bars, confectionery, bakery products, crackers, cookies, biscuits, cereal chips, snack products, infant and baby foodstuff, bread, croissants, spreads, sugar-free biscuits and chocolates, calcium chews, meat products, sausages, mayonnaise, dressings, nut butter, deep-frozen meals, sauces, gravy, soups, shortenings, canned foods and ready-to-serve meals.
18. Foodstuff, characterized in that during its manufacturing process a homogeneous composition according to one of claim 7-12 is added as a constituent.
19. Cosmetic preparation, characterized in that during its manufacturing process a homogeneous composition according to one of claims 7-12 is added as a constituent.
EP09717886A 2008-03-07 2009-03-06 Use of alternan as fat or oil replacer in foodstuffs Active EP2252165B9 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP12169201.6A EP2491798B1 (en) 2008-03-07 2009-03-06 Use of alternan as emulsifier in foodstuffs and cosmetics
EP09717886A EP2252165B9 (en) 2008-03-07 2009-03-06 Use of alternan as fat or oil replacer in foodstuffs
DK12169201.6T DK2491798T3 (en) 2008-03-07 2009-03-06 Use of alternan as emulsifier in food and cosmetics

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP08102410A EP2100517A1 (en) 2008-03-07 2008-03-07 Use of alternan as texturizing agent in foodstuffs and cosmetics
US6889408P 2008-03-11 2008-03-11
EP09717886A EP2252165B9 (en) 2008-03-07 2009-03-06 Use of alternan as fat or oil replacer in foodstuffs
PCT/EP2009/001760 WO2009109407A2 (en) 2008-03-07 2009-03-06 Use of alternan as texturizing agent in foodstuffs and cosmetics

Related Child Applications (2)

Application Number Title Priority Date Filing Date
EP12169201.6A Division-Into EP2491798B1 (en) 2008-03-07 2009-03-06 Use of alternan as emulsifier in foodstuffs and cosmetics
EP12169201.6A Division EP2491798B1 (en) 2008-03-07 2009-03-06 Use of alternan as emulsifier in foodstuffs and cosmetics

Publications (3)

Publication Number Publication Date
EP2252165A2 true EP2252165A2 (en) 2010-11-24
EP2252165B1 EP2252165B1 (en) 2012-06-13
EP2252165B9 EP2252165B9 (en) 2012-09-26

Family

ID=39537960

Family Applications (3)

Application Number Title Priority Date Filing Date
EP08102410A Withdrawn EP2100517A1 (en) 2008-03-07 2008-03-07 Use of alternan as texturizing agent in foodstuffs and cosmetics
EP09717886A Active EP2252165B9 (en) 2008-03-07 2009-03-06 Use of alternan as fat or oil replacer in foodstuffs
EP12169201.6A Active EP2491798B1 (en) 2008-03-07 2009-03-06 Use of alternan as emulsifier in foodstuffs and cosmetics

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP08102410A Withdrawn EP2100517A1 (en) 2008-03-07 2008-03-07 Use of alternan as texturizing agent in foodstuffs and cosmetics

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP12169201.6A Active EP2491798B1 (en) 2008-03-07 2009-03-06 Use of alternan as emulsifier in foodstuffs and cosmetics

Country Status (15)

Country Link
US (2) US9370203B2 (en)
EP (3) EP2100517A1 (en)
JP (1) JP5461440B2 (en)
CN (2) CN101965133B (en)
AR (1) AR070817A1 (en)
AU (1) AU2009221478B2 (en)
BR (1) BRPI0910256A8 (en)
CA (1) CA2717179C (en)
CO (1) CO6280595A2 (en)
DK (2) DK2252165T3 (en)
ES (2) ES2481041T3 (en)
MX (1) MX2010008907A (en)
NZ (2) NZ599071A (en)
SG (1) SG185987A1 (en)
WO (1) WO2009109407A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR112012029519A2 (en) * 2010-05-04 2015-09-08 Cargill Inc fat replacers and filler materials.
US9926541B2 (en) 2014-02-14 2018-03-27 E I Du Pont De Nemours And Company Glucosyltransferase enzymes for production of glucan polymers
EP3237455B1 (en) 2014-12-22 2020-03-04 DuPont Industrial Biosciences USA, LLC Polysaccharide compositions for absorbing aqueous liquid
EP3253454B1 (en) * 2015-02-06 2020-04-22 DuPont Industrial Biosciences USA, LLC Colloidal dispersions of poly alpha-1,3-glucan based polymers

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2050464C (en) 1991-08-30 1997-12-16 Tsutomu Harada Food containing fructose
US5789210A (en) * 1993-11-08 1998-08-04 Purdue Research Foundation Recombinant yeasts for effective fermentation of glucose and xylose
PL180543B1 (en) * 1993-11-09 2001-02-28 Du Pont Fructose accumulating transonic cultivable plants and methods of obtaining such plants
US5702942A (en) 1994-08-02 1997-12-30 The United States Of America As Represented By The Secretary Of Agriculture Microorganism strains that produce a high proportion of alternan to dextran
JPH08154599A (en) * 1994-12-06 1996-06-18 Ajinomoto Co Inc Paste containing furcellaran and used for food, its production and food containing the same
US6833491B2 (en) * 1996-02-07 2004-12-21 D. J. Van Der Have B.V. Modification of polysaccharides
DE19905069A1 (en) * 1999-02-08 2000-08-10 Planttec Biotechnologie Gmbh Alternansucrase encoding nucleic acid molecules
US6602994B1 (en) * 1999-02-10 2003-08-05 Hercules Incorporated Derivatized microfibrillar polysaccharide
DK1409708T3 (en) * 2001-07-20 2010-08-16 Tno Uses of a glucan derived from lactic acid bacteria as anti-corrosion agent
US6479275B1 (en) * 2001-07-25 2002-11-12 The United States Of America As Represented By The Secretary Of Agriculture Penicillium isolates for modifying alternan
US20040052915A1 (en) 2002-09-13 2004-03-18 Carlson Ting L. Use of low glycemic index sweeteners in food and beverage compositions
CA2559470A1 (en) 2004-03-17 2005-09-29 Cargill, Incorporated Low glycemic sweeteners and products made using the same
JPWO2006009259A1 (en) * 2004-07-23 2008-07-31 三栄源エフ・エフ・アイ株式会社 Composition containing hydrogel component derived from gum arabic
US20060093720A1 (en) * 2004-10-28 2006-05-04 Ed Tatz Pumpable, semi-solid low calorie sugar substitute compositions
US7524645B2 (en) 2004-12-14 2009-04-28 Centre National De La Recherche Scientifique (Cnrs) Fully active alternansucrases partially deleted in its carboxy-terminal and amino-terminal domains and mutants thereof
CA2597886C (en) * 2005-02-15 2016-01-26 Cargill, Incorporated Methods of making syrups
WO2007128559A2 (en) 2006-04-28 2007-11-15 Bayer Cropscience Ag Inulin of very high chain length
WO2008051760A2 (en) 2006-10-19 2008-05-02 King Pharmaceuticals Research And Development, Inc. Combination therapy for the treatment of pain
ES2438001T3 (en) 2007-02-14 2014-01-15 Bayer Cropscience Ag Nucleic acid molecules encoding truncated alternating sucrose
EP2350134B1 (en) 2008-10-17 2016-11-23 Bayer Intellectual Property GmbH Alternan derivatives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2009109407A2 *

Also Published As

Publication number Publication date
CN103392954A (en) 2013-11-20
DK2491798T3 (en) 2014-07-28
WO2009109407A3 (en) 2009-11-19
AU2009221478A1 (en) 2009-09-11
BRPI0910256A2 (en) 2015-09-01
ES2386696T3 (en) 2012-08-27
CO6280595A2 (en) 2011-05-20
DK2252165T3 (en) 2012-09-10
MX2010008907A (en) 2010-09-07
AU2009221478B2 (en) 2014-07-31
EP2252165B9 (en) 2012-09-26
US10463606B2 (en) 2019-11-05
JP2011512826A (en) 2011-04-28
US20160278420A1 (en) 2016-09-29
CN103392954B (en) 2015-08-19
NZ587797A (en) 2012-05-25
US20110065810A1 (en) 2011-03-17
CN101965133B (en) 2014-08-13
SG185987A1 (en) 2012-12-28
CA2717179C (en) 2017-01-03
ES2481041T3 (en) 2014-07-29
AR070817A1 (en) 2010-05-05
US9370203B2 (en) 2016-06-21
EP2491798B1 (en) 2014-04-23
WO2009109407A2 (en) 2009-09-11
EP2491798A1 (en) 2012-08-29
CA2717179A1 (en) 2009-09-11
CN101965133A (en) 2011-02-02
JP5461440B2 (en) 2014-04-02
EP2252165B1 (en) 2012-06-13
NZ599071A (en) 2012-11-30
EP2100517A1 (en) 2009-09-16
BRPI0910256A8 (en) 2016-03-22

Similar Documents

Publication Publication Date Title
RU2366278C2 (en) Soluble food fiber of oat and barley grain, production method of fraction enriched with beta-glucan and usage of this fraction in food, pharmaceutical and cosmetics products
US20120135125A1 (en) Concentrated, creamy to solid and dry compositions of an oil-in-water emulsion, method for the production thereof and use thereof for producing improved foods in terms of sensory aspects and nutrition physiology
DE60219600T2 (en) PRODUCTS CONTAINING G (b) -glucan
TWI439232B (en) Soluble oat or barley flour and method of making utilizing a continuous cooker
US10463606B2 (en) Use of alternan as texturizing agent in foodstuffs and cosmetics
JP5321028B2 (en) Food properties improver
JP2002241784A (en) beta GLUCAN-CONTAINING OIL AND FAT COMPOSITION
JP4994336B2 (en) Bread
JP5089644B2 (en) Dough or bread
AU2013202754B2 (en) Use of alternan as texturizing agent in foodstuffs and cosmetics
BRPI0910256B1 (en) USES OF ALTERNAN AS A TEXTURIZATION AGENT IN FOOD INGREDIENTS, HOMOGENEOUS COMPOSITIONS, ITS PREPARATION METHOD AND ITS USES
CA3234327A1 (en) Cheese-like food product
WO2023066879A1 (en) Fresh cacao pod husk derived pectin, method of its preparation and its use in food, pharmaceutical and cosmetic compositions
Farahmand Utilization of inulin as fat replacer in cake and mayonnaise
JP2013172667A (en) Binding property improver for baked confectionery
JP2019076073A (en) Baked confectionery dough

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20101007

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL BA RS

17Q First examination report despatched

Effective date: 20110209

DAX Request for extension of the european patent (deleted)
GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

RIC1 Information provided on ipc code assigned before grant

Ipc: A23C 9/137 20060101ALI20111130BHEP

Ipc: A23D 7/005 20060101ALI20111130BHEP

Ipc: A23L 1/054 20060101AFI20111130BHEP

Ipc: A23L 1/24 20060101ALI20111130BHEP

Ipc: A23L 1/308 20060101ALI20111130BHEP

RTI1 Title (correction)

Free format text: USE OF ALTERNAN AS FAT OR OIL REPLACER IN FOODSTUFFS

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK TR

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: AT

Ref legal event code: REF

Ref document number: 561579

Country of ref document: AT

Kind code of ref document: T

Effective date: 20120615

Ref country code: CH

Ref legal event code: EP

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: DE

Ref legal event code: R096

Ref document number: 602009007563

Country of ref document: DE

Effective date: 20120809

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2386696

Country of ref document: ES

Kind code of ref document: T3

Effective date: 20120827

REG Reference to a national code

Ref country code: NL

Ref legal event code: T3

REG Reference to a national code

Ref country code: DK

Ref legal event code: T3

REG Reference to a national code

Ref country code: SE

Ref legal event code: TRGR

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CY

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20120613

Ref country code: NO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20120913

Ref country code: LT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20120613

REG Reference to a national code

Ref country code: LT

Ref legal event code: MG4D

Effective date: 20120613

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LV

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20120613

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20120914

Ref country code: SI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20120613

Ref country code: HR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20120613

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: RO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20120613

Ref country code: IS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20121013

Ref country code: CZ

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20120613

Ref country code: EE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20120613

Ref country code: SK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20120613

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: PT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20121015

Ref country code: PL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20120613

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed

Effective date: 20130314

REG Reference to a national code

Ref country code: HU

Ref legal event code: AG4A

Ref document number: E015257

Country of ref document: HU

REG Reference to a national code

Ref country code: DE

Ref legal event code: R097

Ref document number: 602009007563

Country of ref document: DE

Effective date: 20130314

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BG

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20120913

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MC

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20130331

REG Reference to a national code

Ref country code: IE

Ref legal event code: MM4A

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20130306

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20120613

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 7

REG Reference to a national code

Ref country code: DE

Ref legal event code: R081

Ref document number: 602009007563

Country of ref document: DE

Owner name: BAYER INTELLECTUAL PROPERTY GMBH, DE

Free format text: FORMER OWNER: BAYER CROPSCIENCE AG, 40789 MONHEIM, DE

Effective date: 20150204

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: TR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20120613

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20120613

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20130306

REG Reference to a national code

Ref country code: CH

Ref legal event code: PUE

Owner name: BAYER INTELLECTUAL PROPERTY GMBH, DE

Free format text: FORMER OWNER: BAYER CROPSCIENCE AG, DE

REG Reference to a national code

Ref country code: GB

Ref legal event code: 732E

Free format text: REGISTERED BETWEEN 20160107 AND 20160113

REG Reference to a national code

Ref country code: FR

Ref legal event code: TP

Owner name: BAYER INTELLECTUAL PROPERTY GMBH, DE

Effective date: 20160107

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 8

REG Reference to a national code

Ref country code: NL

Ref legal event code: PD

Owner name: BAYER CROPSCIENCE AG; DE

Free format text: DETAILS ASSIGNMENT: VERANDERING VAN EIGENAAR(S), OVERDRACHT; FORMER OWNER NAME: BAYER CROPSCIENCE AG

Effective date: 20151208

REG Reference to a national code

Ref country code: ES

Ref legal event code: PC2A

Owner name: BAYER INTELLECTUAL PROPERTY GMBH

Effective date: 20160801

REG Reference to a national code

Ref country code: HU

Ref legal event code: FH1C

Free format text: FORMER REPRESENTATIVE(S): DR. FEHERVARI FLORA, DANUBIA SZABADALMI ES JOGI IRODA KFT., HU

Representative=s name: DANUBIA SZABADALMI ES JOGI IRODA KFT., HU

Ref country code: HU

Ref legal event code: GB9C

Owner name: BAYER INTELLECTUAL PROPERTY GMBH, DE

Free format text: FORMER OWNER(S): BAYER CROPSCIENCE AG, DE

REG Reference to a national code

Ref country code: NL

Ref legal event code: PD

Owner name: BAYER INTELLECTUAL PROPERTY GMBH; DE

Free format text: DETAILS ASSIGNMENT: VERANDERING VAN EIGENAAR(S), OVERDRACHT; FORMER OWNER NAME: BAYER INTELLECTUAL PROPERTY GMBH

Effective date: 20160629

REG Reference to a national code

Ref country code: AT

Ref legal event code: PC

Ref document number: 561579

Country of ref document: AT

Kind code of ref document: T

Owner name: BAYER INTELLECTUAL PROPERTY GMBH, DE

Effective date: 20161206

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 9

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 10

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20230221

Year of fee payment: 15

Ref country code: DK

Payment date: 20230314

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 20230227

Year of fee payment: 15

Ref country code: IT

Payment date: 20230228

Year of fee payment: 15

Ref country code: BE

Payment date: 20230224

Year of fee payment: 15

P01 Opt-out of the competence of the unified patent court (upc) registered

Effective date: 20230507

REG Reference to a national code

Ref country code: NL

Ref legal event code: PD

Owner name: BAYER CROPSCIENCE AKTIENGESELLSCHAFT; DE

Free format text: DETAILS ASSIGNMENT: CHANGE OF OWNER(S), ASSIGNMENT; FORMER OWNER NAME: BAYER INTELLECTUAL PROPERTY GMBH

Effective date: 20230630

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: ES

Payment date: 20230406

Year of fee payment: 15

Ref country code: CH

Payment date: 20230401

Year of fee payment: 15

REG Reference to a national code

Ref country code: DE

Ref legal event code: R081

Ref document number: 602009007563

Country of ref document: DE

Owner name: BAYER CROPSCIENCE AKTIENGESELLSCHAFT, DE

Free format text: FORMER OWNER: BAYER INTELLECTUAL PROPERTY GMBH, 40789 MONHEIM, DE

REG Reference to a national code

Ref country code: GB

Ref legal event code: 732E

Free format text: REGISTERED BETWEEN 20230907 AND 20230913

REG Reference to a national code

Ref country code: BE

Ref legal event code: PD

Owner name: BAYER CROPSCIENCE AKTIENGESELLSCHAFT; DE

Free format text: DETAILS ASSIGNMENT: CHANGE OF OWNER(S), OTHER; FORMER OWNER NAME: BAYER INTELLECTUAL PROPERTY GMBH

Effective date: 20230810

REG Reference to a national code

Ref country code: AT

Ref legal event code: PC

Ref document number: 561579

Country of ref document: AT

Kind code of ref document: T

Owner name: BAYER CROPSCIENCE AKTIENGESELLSCHAFT, DE

Effective date: 20230911

REG Reference to a national code

Ref country code: HU

Ref legal event code: GB9C

Owner name: BAYER CROPSCIENCE AKTIENGESELLSCHAFT, DE

Free format text: FORMER OWNER(S): BAYER CROPSCIENCE AG, DE; BAYER INTELLECTUAL PROPERTY GMBH, DE

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 20240226

Year of fee payment: 16

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: AT

Payment date: 20240226

Year of fee payment: 16

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: HU

Payment date: 20240314

Year of fee payment: 16

Ref country code: FI

Payment date: 20240315

Year of fee payment: 16

Ref country code: DE

Payment date: 20240220

Year of fee payment: 16

Ref country code: GB

Payment date: 20240222

Year of fee payment: 16